


Assassins and Thieves

by AssassinsAndAngels



Category: Elder Scrolls, Elder Scrolls V: Skyrim
Genre: Assassin Dragonborn, Canon-Typical Violence, Dark Brotherhood Questline, F/M, Slight canon deviation, Thieves Guild
Language: English
Status: In-Progress
Published: 2020-08-22
Updated: 2020-11-10
Packaged: 2021-03-06 15:09:06
Rating: Mature
Warnings: Graphic Depictions Of Violence
Chapters: 6
Words: 13,325
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26050930
Author URL: https://archiveofourown.org/users/AssassinsAndAngels/pseuds/AssassinsAndAngels
Summary: When a contract brings her into the Thieves Guild, Octavia is unsure of what to think. She was never made to be a thief, just an assassin. She thinks.When Brynjolf brings the new member of the Thieves Guild into the fold, he has no idea what to think. She's almost better than him, and her skill with a blade impresses him. But he knows she's not telling him everything.Or: Octavia's an assassin, and Brynjolf is screwed.
Relationships: Brynjolf (Elder Scrolls)/Original Female Character(s), Brynjolf/Dovahkiin | Dragonborn, Brynjolf/Female Dovahkiin | Dragonborn, female assassin dragonborn
Comments: 30
Kudos: 56





	1. Chapter 1

“Delvin Mallory?” A woman’s voice seemed to appear from thin air. Brynjolf watched everyone whip their heads around to view the source of the voice. It was only then that he lazily turned his head to view the young woman.

Her strong voice didn’t match her body. The woman was short, at least compared to him. She was, however, carrying herself with confidence that almost made Brynjolf himself jealous. What made him nervous was her armor. The red and black light armor was unmistakable Dark Brotherhood. And to think he heard they were wiped out. It served him right for trusting the rumors. 

“I didn’t expect to ever see you again.” Was Delvin’s response. Brynjolf furrowed his brows. Delvin was their only contact to the Brotherhood, but he thought he only dealt with Astrid. Astrid he had seen a few times, and this woman was not her. 

“Most don’t.” She cryptically answered. Her face was hidden by her cowl, but Brynjolf would bet she was smirking under the hood. 

“Maven was furious when she heard you were gone. That one liked to summon your services whenever we wouldn’t provide her a service.” Delvin’s eyes were calculating. He was sizing her up, as were most of the people in the Flagon. 

“You would do well not to let her know that we survived.” Her voice turned from businesslike to threatening faster than Maven herself could. 

“She’s our biggest provider. Why wouldn’t we?” Delvin narrowed his eyes. The woman seemed to regard him for a moment before standing back up. He hadn’t even noticed she had leaned over. 

“I am now the Listener of the Dark Brotherhood. That means I decide what contracts happen, and how they happen. If you want someone dead, you perform the black sacrament.” She addressed everyone in the room. “Astrid strayed from the path of the Brotherhood. No longer do her rules apply. As I recall,” She leaned back down, resting her hands on the table. “We were the other half of Maven’s power. Where does her power stand if the Brotherhood refuses to back her?” She let the question settle in everyone’s mind. Of course, she was right. The guild would only go so far, and without the two factions she was just another businesswoman. 

“Well then. What can I do for you?” Delvin appeared collected on the outside, but Brynjolf knew him. He had always been close with Astrid, and the change would be a hard hit to Maven. Delvin was angry. 

“I need furnishings for the second sanctuary in Skyrim.” She said no more, but Delvin sighed before pulling out a piece of parchment. “Will twenty thousand gold be enough?” Almost everyone went slack-jawed. The guild hadn’t seen that kind of money in decades! Mercer was going to be pleased. 

“I suppose. Mind me asking where you managed to get all of this coin, given recent events?” Once again, the woman seemed to consider her surroundings before standing back up. 

“Titus Mede the Second was slain by my hand. The Brotherhood is no longer the shadow of its former glory. I fully intend on restoring it.” With a curt nod towards Delvin, she turned and briskly began walking towards the Ratway door. As soon as she was gone everyone in the flagon let out a breath. 

“Maven is going to be beyond angry.” Vex commented, leaning over Delvin to look at the paper he had pulled out. “Think she’ll actually give us twenty thousand?” Delvin nodded slowly, a frown evident on his face. 

“That one always does. Saw her a few times while Astrid was still alive. Pure business, every time.” Delvin replied. 

“What makes you think Astrid is dead?” One of their newer recruits, Rune, asked. Delvin and Vex both chuckled, the sound doing little to disperse the lingering tension. 

“Astrid would only give up her power if she were dead. Seeing as that woman seems to be gripping the Brotherhood tightly, she has to be gone.” Delvin’s face was back to pure business, as normal. 

“I’ll bet Maven storms down here in less than a day.” Tonillia was trying (and failing) to hide a smirk. 

“No, lass.” Brynjolf interjected. “She won’t know until her letters are ignored. Then she’ll come down here and demand we pick up their slack.” Everyone grew silent at that. They weren’t murderers. But Maven was their only true source of coin, and Mercer was known for being less than merciful. 

“Damn.” Was all Vex said, before returning to leaning against her usual pile of boxes. Brynjolf sighed. 

“I’m going to the market.” He said quickly, before walking quickly towards the Cistern. He needed a drink that didn’t come from Vekel. And some time alone. The tiny woman had just wreaked hell on their guild without even knowing it. Or maybe she did know it, he decided. It wouldn’t be like the Brotherhood to care. 

Now donning a set of simple leather armor, he strolled towards the inn. Nothing was different than any other day. Riften was boring,the guild being the only thing that made Riften interesting. Even that could get boring at times. He hummed a tune under his breath. 

“Watch it!” He ran into a small woman, wearing a set of lovely elven armor. She was an Imperial, with jet black hair and stormy grey eyes. What he noticed first, however, was that though he had ran into the Imperial, a redheaded Nord had been the one to admonish him. 

“Iona!” The Imperial scolded. “It’s not a big deal, it was an accident.” She turned to look at the Nord, before sighing. 

“As you say, my Thane.” Woah. Thane? The thought almost made him take two steps back. He hadn’t been aware that there was a Thane in Riften. There hadn’t been in years! The Imperial gave her housecarl a look that told him she didn’t want to be vocal about it. The gears in his brain began whirring. He needed to know what was happening here. 

“No, your housecarl is right!” Brynjolf smiled charmingly. “I should have looked where I was going. Apologies, Thane.” The Imperial sighed. “Could I buy you a drink to make up for it?” She gave him a calculating look before nodding. 

“It would be rude of me to deny such a gift. Iona, would you be so kind as to meet me back home?” With a curt nod, Iona was soon out of sight. Brynjolf held out his arm, allowing the woman to link hers through it. 

“My apologies for being so rude. I haven’t introduced myself. My name is Brynjolf.” he smiled down at her. Being so formal felt odd to him, though he knew that being a Thane meant she had a noble upbringing. Most likely. 

“It’s fine.” She waved her hand. “I’m Octavia.” 

“No surname?” He asked. That was unusual for a woman of her status. She shook her head, smiling at him as he opened the door to the Bee and the Barb for her. She led the way in, sitting lightly down at a secluded corner table. She didn’t offer an explanation, choosing to simply study the other patrons. 

She made excellent conversation. It was lighthearted, and he realized she avoided talking about anything remotely personal, instead answering his questions with questions of her own. Despite that, Brynjolf found himself having fun. However, after three rounds he realized how dark it was. 

“I hate to cut this short, but I really must get going.” He said quickly. She studied him for a moment before nodding. In one swift movement, she pulled a small coin purse out of her pocket and tossed it to Keerava. He raised an eyebrow. “I thought I was supposed to be buying you drinks?” 

“Were you? I suppose you’ll just have to make it up to me tomorrow night.” Octavia winked at him before standing up. Brynjolf laughed, nodding. 

“That could be arranged.” He acknowledged. 

“Good. I look forward to it.” She smiled before strutting out of the inn, presumably towards her house. The woman was by no means a proper noble. She had drunk far too much than would be considered proper, and her banter was not that of a woman who had been raised to be seen and not heard. 

There were two ways one was made Thane in Riften. One could be of noble birth, and have connections to the Black-Briars, or they could do lots of killing for the Jarl. Based on what he had seen, he would bet it was the latter. 

He abruptly stood up, walking briskly back towards the guild. Finally, there was someone interesting in the Hold. 


	2. Chapter 2

After not so subtly threatening the guild, Octavia was in a good mood. Humming to herself as she came up from the Ratway, she immediately shrank into the shadows. It would do no good to get caught in her Brotherhood armor. Especially since she had a meeting with the Jarl and her steward. 

Creeping along, she finally made it to the garden of the abandoned house. Honeyside, she believed. It didn’t matter. No guards paid any attention to the abandoned garden. Though she had to admit, if she had been allowed to take care of it, it would be a welcome sight against Babette’s garden of doom. 

Sliding her Brotherhood armor into the pockets of the newer Elven armor she had acquired, she stepped back out onto the street, smiling at Madesi, Balimund, and Mjoll. She had greatly enjoyed the irony of helping the woman who hated the thieves guild. Bounding up the steps of the keep, she ignored the sneers of the Jarl’s brother as she approached her. 

“My Jarl, I have done as you asked and helped your people.” She kneeled in front of Jarl Laila, who smiled down at her. 

“Stand, child. Then By my right as Jarl, I grant you the name of Thane.” Laila smiled, and Octavia grinned up at her in return. Her steward leaned in, whispering something in the Jarl's ear. Laila nodded, before turning her attention back to Octavia. “I have also found my solution to the matter of Honeyside. It is my gift to you, Thane, along with Iona, your personal housecarl.” A red haired Nord stepped forward, greeting her with a customary head nod. 

“Thank you, My Jarl.” Octavia grinned. Wasn’t this perfect? Not only could she finally have a house for herself, but she had a housecarl to take care of it! 

When all of the pleasantries were done, Iona followed her from the keep. She was quiet, with a seemingly permanent sneer. She began talking with the woman, asking her about day to day like in Riften. In response, the woman asked her how she would best be of use. She did not sound displeased when Octavia told her she would probably just guard her house, and be otherwise free to do as she pleased. 

“Watch it!” Iona snapped as Octavia found herself colliding with someone. Blinking, she pulled away to find the redheaded man from the Flagon. She tried to hide a smirk. He had been watching her carefully from the moment he saw her. 

“Iona!” She turned to her housecarl. “It’s not a big deal, it was an accident!” Iona furrowed her brows, but nodded her head. 

“As you say, my Thane.” Iona nodded again. Octavia turned back to the red haired man, trying not to smile as Iona’s words registered. Weren’t the guild supposed to know everything that happened in Riften? Like a new Thane being appointed?

“No, your houscarl is right!” He smiled in a way that Octavia knew got him almost whatever he wanted. “I should have looked where I was going. Apologies, Thane.” She sighed. It seemed that this was a title that would not escape her now that she had it. “Could I buy you a drink to make up for it?” She regarded him carefully for a moment. 

When the night mother had told her there was a contract on Mercer Frey, she had almost fallen down the stairs. Not only was there a contract, but a specific set of instructions from her unknown client. She had set off for the Guild immediately, not only needing to see Mallory, but also to scope it out. She couldn’t join the guild as an assassin. No, she needed to join as Octavia. Not that she minded. She liked challenges. 

“It would be rude of me to deny such a gift. Iona, would you be so kind as to meet me back home?” With a curt nod, Iona walked briskly towards Honeyside. The man offered her his arm, and began leading her towards the Bee and the Barb. Introducing himself to be Brynjolf, Octavia tried not to grin as she told him her name. With any luck, he would never know that she was the same assassin he had been watching so diligently in the Flagon.

She found that as the night went on she was enjoying his company. Once he stopped trying to charm her using his honeyed words, they bantered almost as friends. She hadn’t giggled like that since before she took over leadership of the Brotherhood. She felt a little bit bad when she nicked his coin purse from him, along with an old looking key. 

His expression when she paid for their drinks was hilarious. So, when he protested, she found herself inviting him out again. 

“I suppose you’ll have to make it up to me tomorrow night.” She watched as a subtle smile slowly grew on his face, until he finally nodded. 

“That could be arranged.” He replied. 

“Good. I look forward to it.” She turned and walked out of the inn, making her way towards Honeyside. She wasn’t displeased with his company, however she would have hoped that he would catch her robbing him. He would know by tomorrow night, she decided. Bidding Iona a good night, she slipped into bed. 

She was right, of course. The next evening he was waiting outside her home, a scowl on his face. She smiled brightly when she saw him. He gave her a once over, seemingly searching her for something before sighing. 

“And here I was thinking you actually enjoyed my company.” He frowned, holding out his hand. “Give me the key.” Raising an eyebrow, Octavia reached into her pocket and pulled out the coin purse and key. 

“I did.” She replied, smirking at him. “But I have to admit, I was wondering if the best thief in Riften would be able to figure out when he was being robbed himself.” He shook his head, rolling his eyes.

“What you did was either stupid or brave, lass.” 

“Why can’t it be both?” She asked. “Let’s go.” She began walking, but was stopped by his hand on her arm.

“Where are you going?” He asked. She nodded in the direction of the inn. “Nope. Not if you’re going to rob me again.” Rolling her eyes, she replied.

“I promise I won’t.” He considered her for a moment.

“Fine. If you’re so bent on drinking with me, meet me in the Ragged Flagon. It’s in the Ratway.” She nodded. “Maybe I’ll see you there.” He frowned at her before turning away. Grinning, Octavia quickly made her way down to the entrance. Of course, it was easy since she had already been down there. But she had to take enough time to make him believe that she had actually had to find it. 

Walking slowly through the tunnels, she finally made her way to the entrance of the Flagon. Delvin and Vex’s eyebrows raised when she entered. Walking briskly towards the bar, she smiled at Vekel before ordering a single water. It was then that Brynjolf entered, eyes widening in surprise when he saw her. 

“Got to admit, I didn’t expect to see you so soon, lass.” He sat down next to her, ordering himself a mead. “How did you make it here so quickly?” Octavia shrugged, taking a sip of her water. 

“Can’t give you all of my secrets.” She said. Brynjolf laughed. 

“Well then. I have a proposition for you.” He said, turning serious. Octavia frowned, before nodding her head for him to continue. “I’d like to offer you a place here in our guild.” The Flagon got almost as silent as when she came the day before. Taking another drink, she pretended as if she were thinking. Of course she would accept. One step closer to taking out Mercer as the Night Mother instructed. 

“What do I need to do?” She asked after a moment. He grinned at her, before instructing her to take care of three people who wouldn’t pay their debt. Nodding, she stood up. 

“Where do you think you’re going? He asked. 

“To deal with them. Don’t worry, I’ll be back in time for us to have our drink.” Shooting another grin over her shoulder, she walked out of the Flagon. She smiled to herself. Getting into the Thieves Guild was much easier than getting into the Dark Brotherhood. She shuddered as she remembered the feeling of waking up to see Astrid balanced so precariously on that bookshelf above her. 

In the end it hadn’t mattered who she killed herself. Astrid had let out the throaty chuckle of hers before knifing the other two. It was unpleasant to watch. Back then she had been new to the art of killing. Now, it seemed to come as easily as walking. It was her second nature. 

That reminded her that she needed to write to Nazir and Cicero. The jester would get worried that something had happened to his Listener, and Nazir would want to know how many contracts the Night Mother had received. A trip back to Dawnstar would probably be more convenient. Not to mention that she needed to give Alya, Adrian, and Alice some contracts. The triplets were always wanting to get out more, but they were far too eager. Wherever they went, more blood than necessary was spilled. Maybe they didn’t need any new ones. 

“Keerava.” She greeted the Argonian as she entered the inn. She received a smile in return, but a frown when she saw the look on her face. “I believe you owe some money to a mutual friend of ours.” Keerava sighed. 

“Normally I would say no. But tales of your power seem to follow wherever you go, and I’d prefer to steer clear of that.” The argonian tossed her a large bag of coins. “Tell Brynjolf to stay out of the inn for a while. You too.” Octavia nodded curtly, before turning on her heel and walking out. Haelga wasn’t as easy to convince. She had to brawl with that one, not that she lost. Still, she didn’t want to get a reputation for fighting everyone in Riften. 

Bersi, at least, was easily persuaded. All it took was a well placed look at the Dwemer urn he had for him to pay up. True to her word, she was back within an hour, and after handing over the money she and Brynjolf had a drink. 

“So, you’ve proven that you’re sneaky. Where did you learn to pickpocket someone like that?” Of course, it was from sneakily pouring poisons into people’s meads. Not that she could tell him that. 

“When you grow up on the streets, you learn what you need to to survive.” She replied. It wasn’t a lie. That’s where she had gotten started, the Brotherhood had just honed everything she knew into perfection. Astrid had once told her she was the gem of their group. Her contracts never needed a follow up of a bail out of jail. 

“I can understand that one, lass.” His smile seemed more genuine this time. He looked less like a cat about to pounce, and more like a normal person. She smiled back. “Our leader asked to see you tomorrow.” Octavia frowned, shaking her head.

“I have an errand to run. I’ll be gone for a week.” She replied. Brynjolf’s smile disappeared. He leaned in closer, speaking at almost a whisper. 

“Mercer doesn’t like being told no. Is there any way you could reschedule your trip?” She shook her head. 

“If he gets annoyed, remind him that having the Thane of Riften in his pocket can’t be anything but good for him. It’s only a week. Then I’ll be back.” She shrugged, and Brynjolf sighed, before leaning back. 

“Right. Where are you going, anyway?” 

“Dawnstar.” She replied. “I have a family that needs me. My brothers and sisters can’t run their business without me, so I have to check in with them from time to time.” Brynjolf frowned again.

“I thought you said you lived on the streets?”

“I did. I didn’t find them until later in life. We aren’t a family by blood, but we take care of eachother. I suppose it’s like your guild.” She motioned around to the few people with them. He hummed thoughtfully. 

“You’re a part of it too now, lass.” Octavia grinned at him. 

“Fair enough. But I need to get back to Honeyside for now, or Iona might storm down here to check on me.” Brynjolf suddenly looked concerned. 

“You didn’t tell her about us?” The sentence shouldn’t have sounded the way it did, but Octavia had to pause to clear her head just the same. 

“Relax. I just told her I wanted to see if the fuss was warranted. She’ll be annoyed when I tell her it’s overrun with skeevers and madmen.” She winked at him, and could have sworn there was the smallest tinge of pink in his cheeks. 

“I hope you’re not referring to me.” She shrugged. 

“I guess you’ll never know. Bye, Brynjolf.” She turned around, not waiting to see if he responded. 

**Notes for the Chapter:**

> I hope you enjoyed this chapter! I've been writing this fic a lot this past week and have lots of ideas on where I'm going to go with it. :)


	3. Chapter 3

“The little bitch will learn to follow my orders or she’s out, Brynjolf!” Mercer was seething. He glared at his second, and Brynjolf had to fight not to squirm under the guildmaster’s gaze. As predicted, Mercer was angry at their newest recruit for saying no to him. Brynjolf, however, was impressed. She was proving herself to be quite the catch. 

Of course, Octavia had barely left his mind for the past three days. He had half a mind to follow her to Dawnstar, but that would only leave himself in a bad position with Mercer and Octavia both. It wasn’t a position he wanted to find himself in. He had a feeling she was just as skilled with a blade as she was thieving. 

No. It wasn’t something he wanted to find out. At least, not by being on the receiving end. He frowned at Mercer.

“Mercer, I assure you, she’s quite the catch. Scared Keerava, Bersei, and Haelga into giving us their money within an hour. Watched her pickpocket a great many people, and she’s the Thane of Riften.” Of course, it had been his pocket she had picked. He couldn’t let Mercer know that, or at the very least he’d be scolded by the man. Mercer rolled his eyes, exhaling loudly before addressing him again.

“Fine. I’ll meet her, but if she fails, it’s on your head.” Brynjolf nodded. She wouldn’t fail. She had come this far faster than even Vex had. She could take whatever Mercer threw at her. Turning, he headed for the exit of the Cistern. It was getting too stuffy down there. 

“You!” The moment he exited the graveyard, he was thrown into the wall by an angry woman. Pinned, he was shocked to find himself looking into the eyes of Octavia’s very intimidating housecarl. “Where is she? I know my Thane has been skulking around with the likes of you, and now she’s packed up and left! Where did she go?” Iona snarled, still pinning his hands to the wall. 

“She didn’t tell you?” That didn’t sound like her. Rough as she was, Octavia would have told her housecarl if she was making a trip halfway across Skyrim. 

“Tell me what?” She asked through gritted teeth. 

“She went to Dawnstar to visit her family.” Brynjolf replied. Normally he would have demanded a fee, but it seemed Octavia and her companions seemed to be getting the drop on him more often than he liked. 

“And why didn’t she tell me?” Her grip loosened, but he still couldn’t move away from the wall. Frowning, he let his head fall against the wall. 

“Did you check Honeyside? She may have left a note.” He said it sarcastically, but it was a true suggestion. Iona narrowed her eyes before letting him go. He rubbed his wrists before looking back up at her. 

“You’re going to come with me, because if I don’t find a note you’re going to be in trouble.” She motioned for him to follow, and against his better judgement he did. In all honesty, he was curious about what her life outside of the guild was like. Obviously she had her little family in Dawnstar, but she was well on her way to making a life for herself here. Iona obviously cared greatly for her. And he would be lying if he said he didn’t care about her as well. Not that he would ever tell anyone that. 

Iona unlocked the door with a key. Just from looking at it, he knew he could open that lock with his pick in a matter of seconds. He resolved himself to getting her a better one later that day, and making two keys for herself and Iona. Iona closed the door behind them before making a beeline for the master bedroom. 

Brynjolf opted to explore the main room. It was small, but decorated with a number of small items. On a mannequin her elven armor was displayed. It suddenly struck him as odd that she would leave her armor. Surely she would not leave on such a trip in her Guild leathers? Frowning, he looked at the chair. He was about to sit down when he heard an exhale of relief, so he followed Iona towards the bedroom. 

It was much neater than he would have expected from her. He also noticed another door, and with a grin he realized it led right outside the gates. He filed it away for if he ever needed to avoid the guards on the way in. Iona cleared her throat, and held out the note for him to read. Though he already knew where she was, he read it. 

_ Iona, _

_ My apologies for not telling you I was leaving. I had urgent business in Dawnstar that could not wait for you to get back last night. I hope to be back within a week, but don’t be worried if it’s a few days more than that. I promise I won’t be alone in Dawnstar- I am visiting family. Take the week off to relax or visit your own family.  _

_ Brynjolf, _

_ I knew she would find you if she didn’t find this letter. My apologies for leaving, and my apologies if I get you in trouble with Mercer. When I get back I will speak with him immediately, if only for your sake. Do try not to take too many other women out for drinks while I’m gone. I was beginning to feel special.  _

_ Thank you both, Octavia. _

Brynjolf chuckled to himself. He could almost hear the teasing note in her voice as he read the last line. Not that he had planned on taking any other women out for drinks. As it happened, she seemed to be the one taking him out more often than not. Handing the letter back to Iona, he noticed the frown on her face. 

“Who is Mercer?” She asked. 

“Just a mutual friend of ours. He happens to run a business on our border with Eastmarch, and she’s been helping us supply him with alchemy ingredients. You’ve seen your garden. We just made a deal, she gives them to me, I give them to Mercer, he sells potions, and we both get a cut of the profit.” The lie slipped off of his tongue so easily that he may have believed himself. Iona simply nodded. 

“I see. I apologize for my earlier behavior. I was worried about my Thane.” Iona acknowledged. Brynjolf just waved it off. 

“I would have been worried too, had I not known she would be gone. Maybe next time you don’t need to pin me against the wall, though?” He grinned at her. 

“I suppose I can refrain myself.” She grinned back. He seemed to have made it onto Iona’s good side now. That would at least make it easier to spend time with Octavia… The thought wormed its way into his head. Since when had he wanted to spend more time with someone like this?

He turned towards the door. It didn’t matter. Quickly excusing himself from the house, he made for the market stands, sighing as he remembered that he still needed to take care of Brand-Shei. He meant to ask Octavia to help, but if he wanted to be spared Mercer’s wrath he would do it sooner. Resigning himself to asking Sapphire or Rune, he moved over towards the inn. Pushing the door open, he found Keerava already staring at him angrily. 

“You have some nerve coming back here with what you and your little friend did.” She glared at him, but handed him a mead nonetheless. It wasn’t even midday, but Brynjolf was beginning to feel like he had a lot on his plate. Octavia, Mercer, Brand-Shei. Not to mention the looming threat of GoldenGlow. Maven would be furious if none of them could do it. At least GoldenGlow was mostly Mercer’s issue. 

He took a long swig of his drink, staring off at the wall. He nearly jumped when Sapphire sat down next to him, ordering herself an ale and sweet roll. Her eyes narrowed as she watched him. 

“I wanted to have a chat with you about our newest recruit.” Sapphire’s eyes were searching him as she watched him. Rolling his eyes, he nodded. “She’s rather suspicious. I was conning the stablehand until she showed up and took his side. Threatened to tell you. I was only trying to gain a bit more coin for us.” Brynjolf sighed. Sapphire wasn’t supposed to be conning people without the guild’s permission, but what could he do about it now. 

“I won’t tell Mercer as long as you stick to the Guild from here on out.” He acquiesced. Sapphire nodded, but her eyes didn’t leave him. 

“I also wanted to ask about the Brotherhood. I heard their new leader found her way down here a few days ago.” Brynjolf nodded slowly. “Maven won’t be pleased. Does this bode well for us, or should I be worried?” Sighing, he ran a hand through his hair. 

Of course they should be worried. Maven preferred the Brotherhood whenever possible. That meant that one of two things would happen. One, Maven’s power would be crippled, so her gold would be as well, or two, they would be asked to do the Brotherhood’s usual jobs. Neither one of those two things was good for them. 

“Don’t worry about it. Mercer and I will handle things.” He said dismissively. He took a drink, enjoying the burn of the alcohol as it slid down his throat. Sapphire continued to regard him with unusual interest. He turned, staring her down until she spoke again.

“The new recruit. Why her?” She was still studying him. Sighing, he once again ran his fingers through his hair. Maybe it was because she was able to pickpocket him. Maybe because she was Thane of Riften. Maybe because she was more fun to talk to than anyone else in the guild, perhaps barring Vekel. Even then, anything you said could be told to another for the right price. 

Of course, for all he knew the same could be said for Octavia. Perhaps she was in Dawnstar telling all of the Guild’s secrets to some Noble with enough coin to rat them out for good. He wrinkled his nose at the thought. She wouldn’t do that. Her eyes were too trusting. Sure, she had seen the horrors of the world. But she wasn’t one to betray her friends. If that’s what she would call him. 

“Watched her pickpocket nearly half of this very inn without getting caught. She only stopped because I was watching her. Figured with the luck we’ve been having, we may as well get a pickpocket like her.” He shrugged, trying to appear nonchalant about it. Sapphire regarded him for another moment before silently getting up, leaving him alone with his thoughts. 

He spent the rest of the week in Eastmarch robbing some Noble of their valuables. Anything to get out of Riften for a while. He loved his family, but he was sick of the worried glances they would throw him whenever he and Mercer got done discussing money. It seemed that every time he thought they would break even, they didn’t. 

Not that anyone could get into the safe. Delvin and himself had to use both of their keys, special ones that didn’t work with normal lockpicks. No, they were just struggling with jobs. Since they give everyone a large cut of what they stole, it made sense that they weren’t breaking even as soon as they had hoped. Soon, they would. 

He was so lost in his thoughts that he barely noticed himself ram into a young woman. Looking down, he frowned at her before seeing the dark hair and cheeky smile that belonged to their newest guild member. 

“Wow Brynjolf. You can’t seem to keep your hands off of me, hmm?” Her shit-eating grin grew even larger as he felt the smallest amount of blood rush to his face. Collecting himself, he finally smirked back before responding. 

“Maybe I don’t want to.” He winked, and was pleased by the blush that rose to  _ her  _ cheeks. She lightly punched his arm, laughing it off. “How was Dawnstar?” The question made her frown. 

“It was fine. I meant it when I said they wouldn’t survive without me. One of my brothers is going, well, mad.” She paused. “Not that he wasn’t already. But he needs my help with the woman we refer to as our mother, so it’s been hard on him.” Brynjolf frowned, and he allowed her to begin leading him towards Honeyside. 

“Why did you leave?” 

“They are all grown adults. Mostly. I want to live my own life outside of them as well. I love them, but I also want a life away from their expectations of me.” She looked up at him, honesty showing in her eyes. 

“So you run from their expectations and towards ours?” She shrugged, before opening the door to Honeyside. 

“Come in?” He did.

**Notes for the Chapter:**

> Happy September :)


	4. Chapter 4

“Alice, the point isn’t to cause pain. Alya isn’t the enemy, and neither is your target. If they haven’t done anything to warrant your malice, make it a clean death that doesn’t end in a trail of blood or bodies.” Octavia frowned at the sisters. Alice was the more bloodthirsty of the three of them, with Adrian being the most kindhearted person she had met. She had a sneaking suspicion that he was only here to look after his sisters, but it was as good of a reason as any. 

“You’re much kinder than Astrid was. She and Arnbjorn enjoyed the pain.” Nazir came up behind her. She turned, nodding her head in greeting. 

“I don’t relish in causing others pain. Death must be brought upon our victims, but there is no need to cause them pain. We will be causing enough in torturing the minds of those who loved them.” She replied. 

“Very eloquent.” He acknowledged. “How goes the thieves guild contract?” She sighed, waving her hand for Alice and Arya to leave them. The two brunettes quickly made their way out. They learned very quickly not to upset the Listener, or the Keeper would be most displeased with them. 

“I have been recruited. The second in command seems to have taken a liking to me. Not that I mind. He makes for good company.” She shrugged, playing with the front strand of her hair as Nazir’s gaze became stern.

“It wouldn’t be good for you to get too involved with the rats of Riften. Don’t forget your duty to us, as well.” He admonished. 

“You would do well not to question me!” Her mental hackles were raised. “I follow the Tenets, not you. If Sithis is displeased by my actions, it will be made known to me so I may correct them.” She glared at him, and the Redguard seemed to shrink in the smallest amount of fear. He then nodded curtly. 

“Of course, Listener.” He said stiffly. She liked Nazir. Really, she did. But in his mind, nothing but the Brotherhood existed. Everyone else were just pawns for him to move about, killing or manipulating as he pleased. If one of the pieces moved too far from what he deemed the correct path… things could get ugly. 

“Send Adrian to me. I have a contract that will suit him.” She said dismissively. He gave her a mock bow before moving away from her. His passive aggressive ways didn’t bother her. It bothered Cicero, though. He despised Nazir, though he had become close with Babette since the fire. Octavia liked to see the jester happy. 

Drumming her nails on the railing, she suddenly jumped the railing, landing with a soft thud on the floor. Drawing her twin daggers, she moved for the straw dummy that was still intact. It seemed they needed five more of them every week. Inhaling, she began placing quick, calculated strikes on the torso, before kicking it back. As it came back toward her, she simply held the dagger out, releasing her tension when she heard the satisfying sound of her dagger piercing the dummy’s abdomen. No, she didn’t like giving her victims pain. But the kill was sometimes one of the most enjoyable things there was. 

“You asked to see me, Listener?” Adrian was a sharp contrast to his sisters, blonde hair with green eyes that were brighter than any she had ever seen. His eyes were currently watching her carefully, as if trying to figure out why she had called him to her. 

“Spar with me.” She said after a moment. There was a brief moment of hesitation, but he nodded before drawing his own daggers. She waited for him to be ready before she drew her own, an ornate set of Daedric daggers. They had been a gift from the Night Mother, waiting in the pockets of one of her victims. 

With a bravery she didn’t know he possessed, he attacked first. Most (Aside from the Keeper) would not dare try their Listener. She easily blocked it, the jab was too high and he was caught off balance. 

“Lower, Adrian.” She instructed. “You only go for the throat if you come from behind. A low jab with your first dagger,” She demonstrated, stopping just short of his abdomen. His eyes widened in surprise for a moment before her next slice came, less than an inch from his throat. “Opens up your attack on the throat.” She put her blades to the side. 

“I thought you said to only go for the throat when coming from behind.” His voice was steady, but his eyes revealed his discomfort. 

“Correct. Going for the throat first is far too obvious for someone wearing our armor.” She smiled at him, motioning for him to set his blades down. He did so, before following her to the Night Mother’s coffin. She looked at the grotesque depiction of their mother, noting that Adrian would not look straight at it. 

“If I may be so bold, may I ask why you wished to speak with me directly?” He asked. His formal tone indicated his background. She had learned from Alya that they were descendents of Nobles from High Rock, and the three Bretons had said nothing of it since. Not that it was her business.

“Nazir and your sisters grow too bloodthirsty. They like drawing the pain from their victims. Babette simply poisons them, and Cicero… well he is Cicero. I do not relish in causing pain, and I do not relish in bringing attention back to our Brotherhood.” She spoke plainly with Adrian, watching as he processed her words.

“You tell this to me why?” 

“I will continue to be gone for extended periods of time. You have noticed that I give out the contracts in a… specific way?” He nodded.

“Babette gets the one’s where the victim is just a victim. Alice and Nazir get the rapists and murderers. Alya and Cicero get the ones in between.” His green eyes sparkled with curiosity. “And I get none.” She nodded. 

“You are exactly like I was when I joined. You want to be here, but you don’t like to cause pain. For you it is your purpose, not your hobby. Am I correct?” He nodded. “I can’t be here to give out contracts. But I expect that my current system is honored. Will you do this for me?” She turned from him, glancing back at the Night Mother. She could feel the approval radiating from the coffin, and it brought a small smile to her lips. She meant it when she said she was going to return the Dark Brotherhood to its former glory. 

“Of course, Listener. Give me the contracts and I will give them to those I deem fit for them.” He said politely. 

“Good. If you wish, you may take some for yourself. But Adrian?” He continued looking at her, cocking his head slightly. “Do yourself a favor and don’t make it an innocent. Our first kills haunt us to the end of our days. Don’t make it someone who doesn’t deserve it.” He searched her for a moment before nodding, excusing himself. 

Retrieving her daggers, she went to find Cicero. It was almost time for her to begin the trip back to Riften, after all. Stopping by her room, she gripped the stack of contracts before depositing them on Adrian’s bed. Straightening up, she turned to find her Keeper lingering in the doorway. 

“Cicero is ready.” Was all he said. Octavia smiled. He had finally ditched the jester outfit for a set of their signature armor, though she noticed with a smile that he kept the gloves. She nodded, and the pair snuck out of the Sanctuary. Mounting the horses she had left near the entrance, they immediately set off for Riften. 

Cicero was to give Delvin the money. If she showed up as both Octavia and an assassin again, she was certain the guild would get suspicious. So Cicero was accompanying her. Not that she minded. He was content to stay silent, unless he went on one of his maddening rants or sang a song. Cicero was safe. Cicero was predictable. Unlike everyone else she had surrounded herself by. Especially Brynjolf. 

The man had certainly intrigued her. While his honeyed words had less of an effect on her than she led him to believe, the fact that he was trying was interesting enough. She was nothing special to the guild, at least, not yet. She smiled to herself as she rode. She would get there, as she did with the Brotherhood. 

When they reached Riften, she sent Cicero ahead to go to the Ratway alone. He nodded dutifully and allowed her to tack both of their horses. Slipping inside the gates, she grinned when she saw the very man she had spent most of the ride thinking about wandering aimlessly around. Grinning, she bumped into him. 

The banter that followed was normal.  _ Safe _ , unlike anything else she did. Inviting him to Honeyside, she spotted Cicero in the shadows. He nodded, signaling that his job was done. She slightly inclined her head in return, then he disappeared into the shadows. Brynjolf followed her inside of her home, and she was unsurprised to see that Iona wasn’t there. 

“Your letter said you would be late, not early.” He jibed. She smiled softly. 

“I’m only a day early. I assume that Iona is in the inn?” He nodded, and she turned to the empty hearth, using the small amount of magic she knew to light the logs on fire. “I hope Mercer wasn’t too hard on you.”

“No harder than usual.” He replied, obviously feigning disinterest. “He was rather annoyed with you, as I recall, so I would be careful with him.” She waved her hand, a gesture that seemed to surprise him. 

“I can handle Mercer Frey.” Was all she said. She had handled worse than him. Harder marks. Images of a dying emporer flashed into her mind, then images of the man who had hired her. Killing him was her favorite kill, though she did so for free. Not to mention that the sum of money he had left her was amazing. She was almost sad that she had to spend it all on the santuary. 

“Good. Because he will want to see you tomorrow.” Brynjolf warned. She suspected that if it hadn’t been nighttime he would want to see her now, but she didn’t bring that up with the redhead. Instead, she pushed a bottle of Honningbrew mead into his hands. He looked at it before looking back, raising his eyebrows. 

“What? You have to admit, it’s better than Maven’s stuff and you know it!” She grinned at him before taking a giant gulp of it. 

“I suppose I can’t argue.” He sighed. He brought the drink to his lips, eyes locked with hers as he took a sip. When he was finished, he took a look around the house. “It seemed darker when I was with Iona.” He commented. That wasn’t what she thought he was going to say. Octavia hummed. 

“Well, I have been told that I can light up a room with my presence!” She winked at him, and was pleased to see the familiar tinge of pink rise to his cheeks before he grinned back. Raising the bottle to her as if to agree, he took another drink. “What’s been happening here in Riften?” She asked. 

“I wouldn’t know.” He responded. At her puzzled look, he elaborated. “I was in Eastmarch on a job. The people there have been getting way too rich. I had to show them who’s the boss.” He smirked as she tilted her head back and laughed. It was true. The people of Eastmarch were too rich. 

“Mostly due to their exploitation of the Argonians and Dunmer.” She countered. “When I last found myself in Windhelm I brawled with a man to get him to increase their pay from eight septims a day to twenty five. That’s still an underpay, considering how much work they do, but the Argonians were grateful nonetheless.” She took another long sip. 

“You certainly are an odd one, Octavia. A thief who goes around advocating for fair pay among others?” She smiled. 

“I can do both. I do my best not to rob a poor man blind, but instead rob the men who have far too much money and not enough to spend it on.” She shrugged. Of course, she had too much money. But she spent a lot of it feeding the poorer citizens of Falkreath until the fire, when she moved on to help Dawnstar. Not to mention she was the unknown donor of thousands to the Honorhall orphanage in the very city she was in. 

“I suppose that’s as noble as we thieves get.” He once again raised his glass to her, and this time she followed suit. They both took a drink, and Octavia found herself remembering how her whole life had really gotten started. 

Grelod the Kind. An old hag that had been terrorizing the children of the orphanage. At the request of another child, she had snuck in and killed the wretched old thing. In response, she had been kidnapped later that week and taken by Astrid. And so her career as a street rat ended, and her career as an assassin began. 

Astrid. Her best friend, the woman who had betrayed her. Astrid, who had burned with the rest. Astrid, whose Blade of Woe now resided in a display case in the Sanctuary, only to be used by the Listener on a contract. Octavia frowned, swirling her drink around in the bottle. It was no good to dwell on the past now.

“Are you alright, lass?” He asked. Her eyes found his and she nodded. 

“Just lost in thought. I’m rather tired.” The request was obvious in her voice, and he nodded before retreating to the door. 

“I’ll leave you to rest, then.” He said quietly. She smiled in thanks, then he was gone. She sighed, downing the rest of her drink before opening her bag of Septims. Counting out two hundred, she quietly left Honeyside, picked the lock on the orphanage’s door, and set the bag down on the table before retreating. 

Typically she sent Adrian to do it. It was normally the perfect job for him. But she was here, and she had brought the money. Sighing, she reached into her cupboard, pulling out a loaf of fresh bread Iona must have bought earlier that day. Ripping off a piece, she put it in her mouth. The action reminded her that she hadn’t eaten all day, and the loaf was soon gone. Making her way to her bed, she fell down onto it. Dreams of a blonde woman and an emperor plagued her mind that night.

**Notes for the Chapter:**

> Sorry it's late!


	5. Chapter 5

“Brynjolf, you’re making us all dizzy. Sit down.” Vex commanded. Indeed, Brynjolf had been walking in circles around the Flagon ever since she left for Goldenglow almost two hours ago. He couldn’t help but be worried for their newest recruit!

Mercer should have never given her that job. Even Vex couldn’t do it, though that might have been for lack of preparation on their part. Still, the island was swarming with mercenaries. Though she looked nimble enough to be good with a blade, he had never actually seen her in action. The thought of her alone on that island at the mercy of some overpaid mercenaries… it didn’t sit right with him. 

He ignored Vex, instead just switching directions. He heard her sigh, but couldn’t bring himself to care. He may be a thief, but he didn’t send people off on suicide missions. Only idiots did that, and he knew he wasn’t one of those. Though he did seem to be finding himself feeling more and more like one the longer Octavia was around. He hated to admit it, but her flirtations were rather flattering. 

If only she hadn’t left for Dawnstar when she did. Mercer was angry at her for ignoring him, and took it out on her by sending her off to Goldenglow. He shouldn’t have allowed it, should have gone himself or at least accompanied her! Groaning, he slammed the mead he had been nursing onto the table Vex had seated herself at before sitting down across from her, stewing angrily. 

“Finally. She’s going to be fine. Don’t know if she’ll complete the job, but she’ll make it out alive. Then she’ll just have to deal with Mercer and Maven.” Vex’s attempt at making him feel better had the opposite effect, and he dropped his head into his arms. “Why’re you so worried about her?” Vex’s eyes had a look in them he didn’t like. 

“I prefer not to send the newest recruits on suicide missions.” He said through gritted teeth. “Like Mercer said last time I talked to him, if she fails her blood is on my hands.” He dropped his head back down, sighing in defeat. He knew there was nothing he could do for her now except wait. 

“So that’s it? You’re just worried because you don’t want to bear the guilt of her death?” Vex exhaled loudly, and when he looked up he could see her rubbing her temple. “That’s more selfish than even I am.” Brynjolf glared at her, but Vex just shrugged. He knew it was true, though. 

“I suppose I’m just a selfish person then.” He mumbled, lifting his head enough to take another drink of his mead. It was all that damned assassin’s fault! If she hadn’t come in here, he wouldn’t have needed a break from the tension-filled Flagon. He wouldn’t have gone to the market, and he definitely wouldn’t have bumped into the newly appointed Thane of Riften. She wouldn’t have invited him for drinks, and someone else would be at GoldenGlow right now.

“You’re the least selfish thief here.” Vex argued. “Look, anyone with half a brain can figure out you have some weird connection with her. There’s nothing wrong with being worried, but by the Divines can you reign it in? Try and look a little bit less like a kicked puppy?” She frowned as he lifted his head again, this time propping it up with his hand.

“First of all, I don’t have a connection with her. I just happen to be responsible for her.” He heard a terribly heard laugh come from behind him, telling him that Delvin had been eavesdropping. “Second of all, I don’t look anything like a kicked puppy.” He leaned back in his chair. “Third of all, how I worry is none of your business.” This time, both Delvin and Vex laughed. Even Vekel chuckled, which only made Brynjolf seeth more. 

“You totally look like a kicked puppy, mae.” Delvin clapped him on the shoulder as he slid into the seat between him and Vex. Frowning at the intrusion, Brynjolf continued to nurse his mead. He needed the alcohol at this point. 

It was barely five minutes later when the door to the Flagon burst open, revealing a figure covered in blood. She had a slight limp as she shoved past dirge before coming to stand right in front of the three thieves. Brynjolf noticed with a start that it was Octavia, and she was holding out a small statue of a bee. 

“How much for it?” Octavia’s voice was strained, and it was then that he noticed the gash on the side of her neck. It looked as if it had only been healed by Restoration magic, and for a moment Brynjolf let himself wonder how many hidden talents the small woman before him had. 

“Been looking for this little beauty. Here, this should cover it.” Delvin handed her a large coin purse, and after peering inside she grunted a ‘thank you’ before collapsing into the final chair of the table. Vekel immediately brought her a healing potion, and she tossed him a few of the gold coins before downing it all in one breath. Immediately she looked better. Her skin regained some of its color, and when she spoke again her voice had returned almost to normal. 

“Thank’s Vekel.” He nodded before returning to his place behind the bar. Octavia took one look at Brynjolf before reaching across the table, finishing the rest of his mead. Vex and Delvin snickered. She held eye contact with him, and he could practically feel the fury radiating off of her. 

“You warned me about the security.” She said, and her calm demeanor somehow frightened him more than if she had yelled. “The difficult locks, and you said they occasionally hired a few mercenaries to patrol.” Vex and Delvin were sitting in shock as Octavia leaned closer to him. “So  _ why was I ambushed by twenty men on my way into the building _ ?” She hissed. Brynjolf unconsciously moved his chair back, and he could feel Delvin and Vex watching him as he held Octavia’s gaze. 

“Lass, I-”

“Don’t  _ Lass  _ me!” She mimicked his voice on the word lass, and it would have been funny if not for the way she was gripping one of the two menacing looking daggers currently seated on her hip. “I was then ambushed by more inside the estate! I’m sneaky,” She paused, inhaling and exhaling. He noted with relief that her grip on her daggers had relaxed. “I’m sneaky, but I can’t sneak past that many guards without an invisibility potion! A warning would have been nice!” She scowled at him before looking at Delvin, now taking his mead and downing it. Delvin sighed, but appeared to not want to argue with the angry Imperial who appeared to be refraining herself from killing Brynjolf. 

“I didn’t know there would be that many guards.” He kept his voice as even as possible, trying not to betray the intense amount of fear he was getting from her anger. 

“Someone did. Otherwise they would have sent someone less expendable instead of me. That’s a big job for an initiation.” Vex’s drink was the next to touch her lips. She didn’t break eye contact with him as she drank, and if she meant to intimidate him, she had achieved the desired effect. 

“I’m sorry, Lass.” He said, and he knew he sounded defeated. 

“Don’t call me that.” She said sharply. “I came here for a break from the murder, and all you’ve done is throw me back into it.” She snarled. Then, all of a sudden, the anger disappeared, replaced by horror. “I have to go.” She stood up abruptly, throwing a final glare at him before rushing out of the Flagon. Everyone watched her go, and Tonilia started laughing the second she was out the door. 

“Oh she got you, Brynjolf!” She cackled. It wasn’t more than a moment before Vex and Delvin joined in, followed by Dirge and Vekel. Suddenly, everyone in the room was laughing at him and he felt more like a fool than ever. 

“Remind me not to get on her bad side!” Delvin grinned as Vekel placed a new mug of mead in front of him, then another in front of Vex. Brynjolf scowled at his own empty mug, frowning as he saw the bloodstain from where her lips had touched it. 

He stood up abruptly. She had no business talking to him like that! He may not have prepared her as well as he should have, but she had embarrassed him in front of the Guild! They may not have all been there, but word travels fast around here. Seething, he set off for the Ratway door, ignoring Vex and Delvin’s worried cries. 

His feet carried them to her door of their own accord. He knew it was dumb of him to show up again so soon after she had clearly made it known that he was not welcome anywhere near him, but his own stubbornness wouldn’t let him stop. He hesitated, arm raised, before knocking on the door. 

A tired looking Iona opened the door. When she saw him she scoffed, but opened the door a bit wider to let him in. Wordlessly, she pointed into the master bedroom before stomping down the stairs to where she resided. Sighing, he quietly made his way over to the doorway. 

“I said I’m fine, Iona.” Octavia looked worse with the armor off. The bloodstained leathers had been tossed to the floor, and though she was no longer drenched in blood, he could see the wounds where her shift didn’t cover. He winced as he took it in. Even her hair was dirty, it was matted together with clumps of dried blood he hadn’t seen in the Flagon. His anger dissipated as he saw her shaking shoulders. 

“I meant it, lass. I didn’t know there would be that many. If I had, I wouldn’t have let you go alone.” She whipped around, her wet eyes flashing with anger again. She stood up, and if fury hadn’t been in her eyes he would have been entranced by the way she practically glided across the floor. As it was, he was rooted to the spot. 

“What part of my speech made you think I wanted you to follow me home?” Her anger was less convincing this time, and it only took Brynjolf a moment to realize she was hiding her hurt. The revelation was worse than her anger. He winced as she moved closer, eyes widening as he was suddenly thrown into the wall, a dagger poised at his throat. 

“Lass, please, I-”

“I told you not to call me that. It is a term of endearment, and you have made it very clear that I am in no way dear to you.” She spat. “Now, I am going to let you go. When you are released, you will have five seconds before my dagger finds itself leaving my hand, aimed wherever I last saw you.” She threatened. “It’s your choice whether it finds my walls or your head.” He nodded blankly, and was let go after a quick shove. He opened the door.

“Lass, I-” 

THUD.

He barely closed the door enough to be missed by the projectile. Scowling, he slammed the door shut. Brynjolf knew he shouldn’t have gone after her so soon. She was angry at him, even if she didn’t know the full story. He turned around, sinking to the ground as he leaned against the door. 

If only she would listen to him for half of a second. If only he could make her understand… He stopped thinking for a moment when he heard the sound of another dagger hitting the door. Then another, and another. A screech of frustration, then silence. He winced as he felt the stillness around him. 

With a huff, he forced himself back to his feet. She would return to the Guild when she was ready. In the meantime, he had to deal with Mercer.

**Notes for the Chapter:**

> Ahaha ~Drama~


	6. Chapter 6

Octavia was beginning to regret taking on a contract that forced her to get to know the ones she would be harming. Mercer was no problem. The man was a prick, and she could see the way he treated the Guild. No, it was the fact that she would be hurting the rest of them. Sighing, her nimble fingers began pulling her hair back into a braid. 

“Hey, sweetroll.” Niruin grinned as she closed the door behind her. She had gotten close to the Bosmer since Goldenglow. They had been assigned by Maven herself to take out Honningbrew Meadery. Turns out killing a raging lunatic and sick skeevers together makes for a pretty good friendship. 

Of course, the nickname came with being his friend. He had one for everyone in the guild, though he would never dare to say it to Vex, Delvin, Brynjolf, or Mercer’s faces. Smiling back, she followed him towards the entrance to the city. It was off to Solitude for them, investigating an old informant of the guild. 

The ride was long. It took nearly three days to get to Solitude, and they spent a full night in the Winking Skeever before attempting to approach the Argonian. It wasn’t until that morning that the pair got up and sat down with him. 

“Galuj-Lei.” They agreed she would do the talking. Niruin had been adamant that they try to scare him into it, and that she was even more intimidating than Mercer himself. Apparently word had gotten around about her outburst to Brynjolf. She hadn’t spoken to him since that night, something that hadn’t gone unnoticed by the rest of the guild. That was almost three weeks ago. 

“I don’t think we have any business.” The Argonian rolled his eyes, tail flicking agitatedly. Octavia pulled on the straps of her dress. The pair had agreed that they would wear street clothes. Guild Leathers were too obvious these days. Octavia narrowed her eyes, before pulling out both pieces of paper she had collected from Goldenglow and Honningbrew. 

“You’re going to tell us who you sold these to.” Her voice held an unspoken threat as she regarded the Argonian carefully. He frowned as he looked over the papers. 

“I only talk to those who have something I want.” He said dismissively. In a flash, Octavia had her knife now on the table, balanced precariously in her hand. Niruin looked around, making sure no one was watching as Octavia leaned in. 

“I have something you want. Your life. I could kill you right now, and we have enough gold to cover the bounty.” She threatened. The knife was now twirling in her hand, doing a horrible but amazing dance as she flipped it around in her dexterous fingers. Gulem-Eui looked between her, the knife, and the paper. 

“Fine!” He threw his hands up. “All I know is a woman approached and had the coin. I set it up and boom! Deal.” Octavia narrowed her eyes, and he shrugged. “In my business, we tend not to ask for names.” It was as if he had known her next question. Niruin made as if to speak, but Octavia held her hand up. 

“Thank you. Your cooperation was very helpful.” Her knife found its way into her pocket, and she pulled Niruin up into their room. “Get your armor on.” She commanded. 

“He knew more!” He protested. “We should have gotten more from him!”

“We will.” She answered. “But I know his type, and that scaly bastard won’t tell us anything else, no matter the coin we promise him. No, we are going to follow him. I’ll bet you anything he’ll go to the East Empire Warehouse.” Niruin gaped at her for a moment before nodding, pulling his own leathers on. 

She was right, of course. They quickly caught up to him just as he was entering the mountain carved building. The Argonian’s tail swished as if he were agitated before letting the door close behind him. His first mistake was not closing it behind him, as in a flash Octavia’s foot was keeping it from latching closed. The two thieves did not make the same mistake, Niruin closing the door behind himself. 

They lost him quickly enough, but Octavia was not perturbed. The dusty shelves full of various odds and ends were quickly cleared of anything worth value and given to Niruin to be kept safe. If things went wrong, she was their fighter, and he was the one to flee to report what happened. Octavia had told him this with no room for discussion. Enough of her kin had died.

Since when had they become her kin? Of course, the Dark Brotherhood would always come first. It was why she was to murder the head of her newfound family. But did she want to be done with the guild after that? If she wanted to stay involved, how would she balance both? She shook her head, clearing it of those thoughts. They weren’t to be dwelled upon. All she knew was that she had to stick with the guild until she met the person who had made the contract. She was told that she would know when she saw them. Sithis would guide her. 

Continuing on, the pair found what seemed to be an office of sorts. Octavia left Niruin to stand guard as she crept up the ledge. She found a few rubies and some gold, along with a giant map that she was almost certain Delvin would appreciate. She quickly made her way back down as Niruin frantically waved at her. 

The guard was too close. She sized him up, but a glance at the ship next to them told her she would not be escaping with her life if she attempted to take him on. There were six more guards on the ship. Instead, she pressed a hand over Niruin’s mouth, pressing herself against him, just outside of the torch's dim light. 

The pair held their breath, Niruins eyes darting between her face and the guard. A few minutes later he moved on and the pair relaxed for a moment before Octavia beckoned him back. They lost the Argonian somewhere behind them. She just needed to find the secret passage he used…

She spotted a tiny alcove with a door in it. She motioned to Niruin to follow her and he did, the pair rolling under the shelves with practiced ease. Niruin picked the lock this time as she stood guard, and it only took a few moments for her to hear the familiar release of the lock. The pair quickly made their way inside, finding themselves in another large cave. 

“Follow me. And keep your bow at the ready.” She whispered. Niruin nodded. She could hear voices up ahead, and she saw Niruin draw his bow. She held up a finger and he nodded, allowing her to dart ahead. Her daggers were out of their sheathes, and with a quick flick of her hands an arrow was shot through one of the man’s throat. Seconds later Octavia was behind the other man, quickly dragging the blade across his throat. She caught him as he slumped down. One person’s body hitting the floor might just be a trip. Two meant intruders. 

Scanning the bodies, she and Niruin each got a coin purse from their respective kills. Octavia could sense that her blades had not seen all of their blood today, so she kept them at the ready, the glint of the blade’s dulled by the remnants of the bandit’s blood. Before they continued Niruin turned to her.

“We aren’t supposed to kill everyone.” He whispered, eyes darting back and forth between her and the bandit. Octavia lowered her weapons for a moment.

“We are in the caves below Solitude. They are massive, they echo, and are almost impossible to sneak through. It’s called Brinewater Grotto.” She had a contract here once. She left that day after having spilled more blood than she meant to. “You can’t leave any enemies behind you here or you’ll get flanked. Besides, these are common bandits. My guess is Gulum-Eui recruited them for something bigger. He can get more.” Niruin nodded uncertainly, but followed her as she continued on. 

They took out many more bandits than she was expecting, along with a few frostbite spiders that would have made short work of her without Niruin. His arrow had pierced the beast’s abdomen just before it struck her. She had thanked him profusely before they continued on. She decided she was lucky he could shoot, because the Bosmer looked ill when they looted the bodies. Killing wasn’t his style, and she supposed they wouldn’t have made it this far if he was relying on melee weapons. 

She spotted the Argonian just ahead, surrounded by three bandits. Sighing, she pulled out her own bow. It was an Ebony one that she had killed a Noble for. At least, she had bought it with the coin the Noble’s contract had gotten her. She preferred her daggers over the bow, but she wasn’t liking the look of the giant warhammers all three men had on them. 

“You take out the one on the left. The guy with the orcish hammer will be more deadly, and harder to get an arrow in. I’ll take out the guy on the right and then go in, but be prepared to get him with an arrow if you can. Anywhere, if it slows him down.” She instructed. Niruin nodded, slowly nocking an arrow. 

“And if he hits you?” She flashed him a grin, her signature one that she knew made her look cocky, but more importantly, dangerous.

“I’d like to see him try.” Three seconds later two of the bandits were dropping to the floor, and before they hit the ground Octavia had taken off running. Her bow was sheathed and her dagger back out by the time she reached him, but he had also drawn the warhammer. Gulem-Eui scrambled backwards as the bandit swang the warhammer at her, but she jumped back with practiced ease. Twirling her dagger in her hand, she grinned at him. She hadn’t had a proper fight in  _ ages _ .

He swung again, but this time she ducked, eyes appraising how he moved. His feet were unbalanced, and her grin grew wider as a plan formed. Something that was certain to end in his death, but fun for her.

She let him keep coming for her as she maneuvered them closer to the water. Her back was to it. Normally such a position would make her nervous, but a quick glance at the button on the wall and the bridge behind her made her confident. Finally, her feet were hitting the edge. She feigned fear as she pretended to stumble backwards, but at the last second she threw the dagger. Not at him, but at the button on the wall. 

The bridge creaked, and for a moment she thought her plan was going to go very sour very fast. But it fell just as she had to jump back to avoid his final swing, and as he was pulling the hammer back up she kicked at his leg, dropping him to one knee. Remembering Adrian as she did it, she plunged her dagger into his abdomen, registering the shock on his face before pulling it out and quickly swiping it across his throat. She wasn’t repulsed by the blood that covered her. No, it brought a thrill she hadn’t felt in a long time.

His blood splattered on her armor and face, she stalked towards the cowering Argonian, who held out a simple iron dagger to defend himself with. Niruin would later tell her that she looked like a cat stalking its prey as she put one foot in front of another, only pausing to retrieve the dagger from its place near the button. 

“Put that away.” She gestured to the dagger. “We both know it will do you no good now.” He sighed as he sheathed it. She motioned for him to stand up, and he did so without hesitation. She suddenly understood him. For him, life was about survival. He was a thief of a different caliber than the guild, playing amongst nobles. He had finally made a mistake, and he would do anything to get out alive so he could begin playing and plotting his next hand. 

“Niruin, search the chests for anything valuable. Whatever operation they had going on here is done.” Niruin would also tell her later that she looked like a cross between an Aedra and a Daedra. Beautiful and terrifying as she wiped the blood from her face, continuing to stare down Gulem-Eui. She regarded him for a moment before speaking again. 

“I don’t want to kill you. You’re useful when you’re not betraying us.” She let the threat hang between them for a moment before continuing. “Your friends are all dead. You’ll have to find new ones, though I suppose it won’t be hard for someone such as yourself.” She frowned at him. “Now. Who bought Goldenglow and Honningbrew?” He gulped before answering. 

“Karliah! It was Karliah!” He exclaimed. She raised an eyebrow, allowing her dagger to dance threateningly across her fingers. 

“You say that name like I’m supposed to recognize it.” He gulped again.

“All I know is that she betrayed the guild in some way! She said to tell whoever found me to meet Mercer at the beginning of the end… please that’s all I know!” Octavia sighed, considering her options. Of course, the darker side of her, the side that was made by the Dark Brotherhood told her to kill him. But that would only anger Mercer, and she was quickly seeing why someone might want him dead. 

“Fine. Breathe a word of what happened here today and you might find yourself being hunted by an assassin instead of a thief.” She threatened. He wouldn’t meet her eyes as he nodded, and Octavia watched as Niruin began pulling a series of levers, the middle one opening up a passage she hadn’t seen. 

With a final threatening look at the Argonian, she followed Niruin out, ignoring the ugly horkers that watched them pass carefully. Niruin continued glancing apprehensively at her as they walked out. 

“Octavia, wait!” Damn. She thought she had a few more minutes to compose herself before he started asking questions. He grabbed her by the arm, and before sh eknew it he was pinned to the wall. Cursing, she let him go. 

“Damn it, Niruin you can’t grab me like that when I’m so tense!” She snapped. SHe suddenly noted the fear in his eyes, and softened. “I’m sorry. I have no reason to be angry with you.” He nodded, but continued to look back and forth between the road they were walking on and her. 

“The guild doesn’t normally slaughter unsuspecting victims, Octavia.” The lack of her nickname worried her. She winced as she thought of how ruthless she had been. How ruthless she had asked him to be. She took a step back, unconsciously putting her hands on her daggers. 

“I’m sorry. Sometimes It’s hard to seperate my past from my present and I lose control. I forget sometimes that I’m a part of the guild now, and not my family.” She frowned. “I meant what I said in there, though. There’s no sneaking through. Though perhaps I should have asked the men in front for passage before killing them.” She admitted with a sigh. Niruin still looked apprehensive as they walked, keeping her at arms length. Literally. 

“Brynjolf and Mercer won’t be happy with us.” Niruin glared at her, though a glare was better than the fear he had given her before. 

“Don’t worry about them. I’m not afraid of Mercer, and I can handle Brynjolf.” SHe said confidently. Niruin let out a small chuckle. 

“Oh, I heard how you handle him. Vex and Delvin made sure the whole guild knew how you embarrassed him after Goldenglow!” She blanched for a second before a slight pink came to her cheeks. She had forgotten how badly she had chewed him out. In front of Vex and Delvin, no less. She had stolen their drinks! 

“By the divines I had almost forgotten about that!” She exclaimed. “I haven’t spoken to any of them in so long.” It was true. Her path didn’t often cross Vex and Delvin, and she was plain avoiding Brynjolf. 

“Yeah, rumor has it Brynjolf chased you to Honeyside and you kicked him out almost immediately. He came back and didn’t speak to anyone for hours.” He informed her. Trying not to to let him know how those words affected her, she stared at the cobbled road. It was worn, the stones chipping in places. 

“He should have warned me. They all should have, but he’s one I actually trusted to have my best interests in mind. My first mistake in regards to him.” She said it airily, waving it off with a flick of her hand. “It doesn’t matter anymore. I’m alive, and doing perfectly fine without him.” Niruin regarded her carefully for a moment. 

“If it doesn’t matter anymore then why do you continue to avoid him?” The Bosmer had a point. Anytime he walked into a room, she quickly excused herself and walked out. He had tried to talk to her a few times, but she had waved him off in favor of anyone else. She knew it hurt him, she would have to be blind not to see it. But it was kind of the point. She knew she was being cruel, but why get close to him if he’s only going to betray her?

“To protect myself in the future.” She answered stiffly. “I won’t be blindsighted like that again. Not by him, not by Mercer, not by anyone.” They had reached the stables, and they both mounted their respective horses. 

She was unaware of the cloaked figure that followed close behind them.

**Notes for the Chapter:**

> Haha it's been too long. In my defense, I've had a lot going on. I finally got a job, dyed my hair (I've decided that black hair suits me) and I've been reading more than writing. But anyways. I hope you enjoyed!


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